Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0438)
Drug Name
Desogestrel
Prodrug Info Desogestrel is the prodrug of 3-Ketodesogestrel
Synonyms
Desogestrelum; Desogestrelum [INN-Latin]; Cerazette; DESOGESTREL; ORG 2969; Org-2969; desogen; (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol; 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol; 18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17alpha)-; 54024-22-5; 81K9V7M3A3; C22H30O; CHEBI:4453; EINECS 258-929-4; HSDB 3593; NCGC00167449-01; UNII-81K9V7M3A3
Indication Female pelvic pain [ICD11: GA34] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 310.5 Topological Polar Surface Area 20.2
Heavy Atom Count 23 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
40973
PubChem SID
9831 ; 7849426 ; 7979047 ; 8176865 ; 12015338 ; 14923366 ; 14923367 ; 24702329 ; 34706666 ; 46505739 ; 48415858 ; 49963130 ; 50112703 ; 53787301 ; 56352943 ; 57312489 ; 71831485 ; 78875517 ; 92717926 ; 103566300 ; 104335749 ; 117391777 ; 126621867 ; 126653606 ; 126671043 ; 134338449 ; 135003936 ; 135727366 ; 136197332 ; 137002814 ; 140504081 ; 144206006 ; 152102617 ; 160963652 ; 162176918 ; 163133991 ; 164152385 ; 164756093 ; 175267238 ; 178103644 ; 179150590 ; 184552366 ; 196105624 ; 206246236 ; 223673205 ; 223974105 ; 226426388 ; 241094430
ChEBI ID
ChEBI:4453
CAS Number
54024-22-5
TTD Drug ID
D06CGB
Formula
C22H30O
Canonical SMILES
CCC12CC(=C)C3C(C1CCC2(C#C)O)CCC4=CCCCC34
InChI
1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
InChIKey
RPLCPCMSCLEKRS-BPIQYHPVSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
13-Ethyl OH-desogestrel DM006585 N. A. Oxidation - Hydrolyzationn 1 [4]
15alpha-OH-desogestrel DM006576
154699940
Oxidation - Hydrolyzationn 1 [4]
16-OH-desogestrel DM006584 N. A. Oxidation - Hydrolyzationn 1 [4]
2-OH-desogestrel DM006579 N. A. Oxidation - Hydrolyzationn 1 [4]
3alpha-OH-desogestrel DM006572
29981456
Oxidation - Hydrolyzationn 1 [4]
3beta-OH-desogestrel DM006575 N. A. Oxidation - Hydrolyzationn 1 [4]
5alpha-Hydrodesogestrel DM006580 N. A. Oxidation - Hydrolyzationn 1 [4]
5beta-Hydrodesogestrel DM006581 N. A. Oxidation - Hydrolyzationn 1 [4]
6alpha-OH-desogestrel DM006582 N. A. Oxidation - Hydrolyzationn 1 [4]
6beta-OH-desogestrel DM006583 N. A. Oxidation - Hydrolyzationn 1 [4]
Desogestrel sulfate DM006578 N. A. Conjugation - Sulfation 1 [4]
15alpha-OH-desogestrel Glucuronide DM006577 N. A. Conjugation - Glucuronidation 2 [4]
3-Ketodesogestrel DM006574
6917715
Oxidation - Oxidationn 2 [4]
Desogestrel conjugates DM006573 N. A. Conjugation - Glucuronidation 2 [4]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007087 Desogestrel 3alpha-OH-desogestrel Oxidation - Hydrolyzationn CYP2C9 ... [4]
MR007090 Desogestrel 3beta-OH-desogestrel Oxidation - Hydrolyzationn CYP2C9 ... [4]
MR007092 Desogestrel 15alpha-OH-desogestrel Oxidation - Hydrolyzationn Unclear [4]
MR007094 Desogestrel Desogestrel sulfate Conjugation - Sulfation Unclear [4]
MR007095 Desogestrel 2-OH-desogestrel Oxidation - Hydrolyzationn Unclear [4]
MR007096 Desogestrel 5alpha-Hydrodesogestrel Oxidation - Hydrolyzationn Unclear [4]
MR007097 Desogestrel 5beta-Hydrodesogestrel Oxidation - Hydrolyzationn Unclear [4]
MR007098 Desogestrel 6alpha-OH-desogestrel Oxidation - Hydrolyzationn Unclear [4]
MR007099 Desogestrel 6beta-OH-desogestrel Oxidation - Hydrolyzationn Unclear [4]
MR007100 Desogestrel 16-OH-desogestrel Oxidation - Hydrolyzationn Unclear [4]
MR007101 Desogestrel 13-Ethyl OH-desogestrel Oxidation - Hydrolyzationn Unclear [4]
MR007093 15alpha-OH-desogestrel 15alpha-OH-desogestrel Glucuronide Conjugation - Glucuronidation UGT [4]
MR007088 3alpha-OH-desogestrel Desogestrel conjugates Conjugation - Glucuronidation UGT ... [4]
MR007089 3alpha-OH-desogestrel 3-Ketodesogestrel Oxidation - Oxidationn HSD [4]
MR007091 3beta-OH-desogestrel 3-Ketodesogestrel Oxidation - Oxidationn HSD [4]
⏷ Show the Full List of 15 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 ClinicalTrials.gov (NCT01482338) Premenstrual Symptoms Treatment Comparing Between Oral Contraceptives Containing Desogestrel and Drospirenone.
2 The role of CYP2C in the in vitro bioactivation of the contraceptive steroid desogestrel. J Pharmacol Exp Ther. 1998 Dec;287(3):975-82.
3 The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. Br J Clin Pharmacol. 2005 Jul;60(1):69-75.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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